Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D277/70—Sulfur atoms
  • C07D277/74—Sulfur atoms substituted by carbon atoms
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/008—Preparations for oily skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/70—Sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D235/28—Sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
  • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
  • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
  • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Definitions

• the subject of the invention are topical, cosmetic preparations for the improvement of the oily and unesthetic appearance of hair and skin, especially for the treatment of very oily hair.
• N,N-diethyl-m-toluamide was recommended as active substance for the treatment of dandruff due to seborrhea in the DE-OS No. 19 06 665.
• phenyl-pentadienoic acids are recommended as agent for the prevention of the production of sebum. But it was found that neither N,N-diethyl-m-toluamide nor phenyl-pentadienoic acid has a satisfactory antiseborrheic effect.
• topical cosmetic preparations with a content of compounds of the general formula: ##STR2## in which R 1 represents an aryl radical or a heterocyclic radical, R 2 and R 3 represent independently of one another hydrogen or an alkyl group with 1 to 4 carbon atoms, and Y an alkoxy group with 1 to 12 carbon atoms, an aralkoxy group or an amino group NR 4 R 5 in which R 4 and R 5 stand for hydrogen, an alkyl group with 1-6 carbon atoms, an aryl group or an aralkyl group or they can form a heterocyclic ring together with the nitrogen atom, are especially effective in the treatment of seborrheic skin and very oily hair.
• R 1 includes radicals of the general formula (II) ##STR3## in which R 6 , R 7 and R 8 represent independently of one another a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, a halogen atom (especially Cl), an aryl group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, or an amino group that may also be alkylated or acylated, and two of the radicals R 6 -R 8 , which, together with the benzene ring, stand for a naphthalene ring, and includes heterocyclic radicals such as a, if needed substituted, pyridyl, pyrimidyl, benzoxazolyl, benzimidazolyl or benzthiazolyl group.
• R 6 , R 7 and R 8 represent independently of one another a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, a halogen atom (especially Cl), an aryl
• Arene-carboxylic acids suitable as starting product are, for example: 2-(Phenyl-, 2-chlorophenyl-, 3-chlorophenyl-, 4-chlorphenyl-, 2,4-dichlorophenyl-, 3,4-dichlorophenyl-, 4-hydroxyphenyl-, 2,4-dihydroxyphenyl-, 3,4-dihydroxyphenyl-, 4-aminophenyl-, 4-acetamidophenyl-, 4-tolyl-, ⁇ -naphthyl-, ⁇ -naphthyl, 4-methoxyphenyl-, 2,4-dimethoxyphenyl-, 3,4,5-trimethoxyphenyl-, 2,4,6-trichlorophenyl-, benzoxazol-2-yl-, 5-chlorobenzoxazol-2-yl-, 5,7-dichlorobenzoxazol-2-yl, benzothiazol-2-yl-,
• Suitable as alcohol component for the preparation of the arene-carboxylic esters are, for example, methanol, ethanol, propanol, isopropanol, N-butanol, isobutanol, sec-butanol, tert-butanol, pentanol, hexanol, octanol, 2-ethyl-hexanol, decanol, benzyl alcohol.
• Suitable as amide component of the amides to be used according to the invention are, in addition to primary amides, for example, methyl-, dimethyl-, ethyl-, diethyl-, propyl-, dipropyl-, methyl propyl-, 2-propyl-, di-2-propyl-, butyl-, dibutyl-, 2-butyl-, sec-butyl-, tert-butyl-, hexyl-, dihexyl-, ethanol-, diisopropanol-amine, benzylamide, anilide, piperidide and morpholide.
• primary amides for example, methyl-, dimethyl-, ethyl-, diethyl-, propyl-, dipropyl-, methyl propyl-, 2-propyl-, di-2-propyl-, butyl-, dibutyl-, 2-butyl-, sec-butyl-, tert-
• the cosmetic agents according to the invention are solutions of the active compounds of Formula (I) to be used in water, in alcohol, in aqueous alcoholic mixtures, in oil, suspensions, gels, emulsions, ointments, pastes or aerosols.
• the antiseborrheic arene-carboxylic acid esters and amides can be incorporated in almost all cosmetic agents normally used for the treatment of skin and hair, for example in hair tonics, shampoos, hair treatments, hair rinses, or also in skin lotions and shaking mixtures.
• the products according to the invention contain known vehicles and adjuvants such as water, organic solvents, surfactants, oils and fats, waxes, perfume oils, pigments, preservatives and similar substances.
• Shampoo is an advantageous form of application for the treatment of very oily hair.
• such shampoos may contain anionic, cationic, nonionic or amphoteric tensides, pigments, fragrances, thickeners or conditioners.
• the cosmetic agents according to the invention contain the arene-carboxylic acid derivatives in an amount of 0.01 to 20 percent by weight, preferably 1 to 10 percent by weight, calculated with regard to the total product.
• the agents according to the invention can be applied daily; but satisfactory results are obtained even with one weekly application.
• the individual dose to be used for each treatment is not critical. Undesirable side effects were not observed.
• the oily appearance of the hair is reduced and renewed oiliness is delayed, which makes normal hair grooming possible.
• a lasting improvement in the appearance of the skin is possible with regular applications according to the invention in the form of skin creams or milk preparations or shaking mixtures.
• the antiseborrheic action of the compounds used in the cosmetic preparations according to the invention was subjected to closer scrutiny in subsequent animal experiments.
• Male Wistar rats weighing 220-230 g were used as experimental animals.
• the degree of brown discoloration on the shaved backs of the rats was visually evaluated.
• the brown discoloration is caused by the brown skin surface lipid of the rats. This test is based on the observation that young female rats as well as male rats after washing with tenside solution or a lipolytic solvent, and also male rats that had been systemically treated with estrogen, have only normal, fair, pink-colored skin showing after shaving; in keeping with this observation, comparatively negligible amounts of lipid can be extracted from the shaved hair.
• test substances were applied each in the form of a 1% solution in ethanol or ethanol/acetone (1:1) by brushing unilaterally on the back hair of groups of six rats.
• the other side was treated only with the solvent minus active substance (control side).
• the first criterion was the evaluation of the correct identification of the treated side by the majority of the panelists. The following differentation was made:
• the second criterion was the determination of the difference between right and left side, for which 1 point could be given per panelist and animal, the darker side being graded 1, the lighter side 0, and in the case of uniform appearance, both sides 0.5 each.
• the third criterion was the additional classification of the differences in the intensity of the brown coloring, using the following scale:
• the third method of evaluation is used to form the differences of the sums of points between the untreated control animals and respectively the treated and untreated sides of the experimental animal groups, significant differences between control animals and the treated side of the experimental animals again denoting the action of a substance.
• topical agents according to the invention for the treatment of very oily hair and seborrheic skin.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Dermatology (AREA)
• Cosmetics (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=6133325

Family Applications (1)

Country Status (6)

Cited By (5)

Family Cites Families (11)

• 1981
  • 1981-05-27 DE DE19813121072 patent/DE3121072A1/de not_active Withdrawn
• 1982
  • 1982-05-20 IT IT21373/82A patent/IT1190832B/it active
  • 1982-05-21 WO PCT/EP1982/000111 patent/WO1982004391A1/en active IP Right Grant
  • 1982-05-21 JP JP57501606A patent/JPS58500807A/ja active Pending
  • 1982-05-21 DE DE8282901512T patent/DE3269588D1/de not_active Expired
  • 1982-05-21 US US06/444,588 patent/US4528286A/en not_active Expired - Fee Related
  • 1982-05-21 EP EP82901512A patent/EP0079899B1/de not_active Expired

Non-Patent Citations (5)

Also Published As

Similar Documents

Legal Events